My desire to take advantage of flight deals and see new places often takes me to destinations I might not have otherwise considered. An $89 round trip flight from Chicago to Louisville, for example, is how I ended up discovering that there’s a lot more to Kentucky‘s Bluegrass region than horses.

Louisville
The Louisville airport is larger than Lexington and receives more daily flights, which means for most people, it will be cheaper to fly into Louisville than Lexington. The two cities are an hour’s drive away from each other, so you can easily see both over a long weekend, no matter which airport you fly into. Louisville is the larger of the two cities- actually it is the largest in Kentucky. It’s not a major city though, and if you come expecting a Bluegrass Chicago, you may be disappointed.

That’s not to say there aren’t plenty of things to do in Louisville though. Boxing fans will want to visit the Muhammad Ali Center and baseball lovers can’t miss the Louisville Slugger Museum and Factory. The West Main area, also known as museum row, is home to several impressive art, history and science museums. Fort Knox and the Belle of Louisville (the oldest Mississippi-style steamboat still in use in the US) are also popular attractions.

In Louisville, I stayed at the 1888 Rocking Horse Manor. A totally restored historic house just south of the downtown area (an easy 15 minute walk), it features its original stained glass, antique furniture, free wi-fi, and a cooked-to-order breakfast included in the rate. The furnishings look a little like they came from your grandma’s house, but the hosts are helpful and friendly, the breakfast (and soft, chewy cookies available all day) is delicious, and the house is full of hidden nooks and crannies where you can escape and relax. Rates start at around $85 per night.

To find Louisville’s trendy scenesters (yes, they do exist), head to Proof on Main, a lounge/restaurant in the 21C Hotel. The menu features artisanal small plates (like bison bone marrow or grilled fennel relish) and eclectic main plates like roasted beet risotto and Amish chicken that start at $15. The drink list emphases the local Bourbon. The $10 Woodland Cider (bourbon, clove and apple cider) was excellent and you can take your drink into the adjoining museum and browse the modern art installations while you sip.

For a more casual meal, check out the pub grub at Bluegrass Brewing. They serve all the standards like burgers, pizzas and salads, plus local specialties like the Hot Brown – a giant sandwich of turkey, tomato, bacon, cheese and Alfredo sauce. After a few Bourbon Barrel Oatmeal Stouts, it’s just the kind of food you may need to avoid a morning hangover.

Lexington
Lexington is pure horse-country. The airport is just outside of Keenland, where you can place your bets and watch athletic Thoroughbred horses speed around the track. True horse enthusiasts (and anyone with kids) should head to the Kentucky Horse Park, a working horse farm, event grounds, and museum dedicated to all things horse. The park is home to over 100 horses (less in winter) and often hosts horse shows and competitions like the Rolex Kentucky 3-Day Event. Admission is $15 for adults and well worth it. Plan on spending at least 3-4 hours onsite. The farm offers horseback and pony rides (as do several other farms in the area). Many racing and breeding farms also offer tours (by appointment) to visitors.

The Bourbon Trail runs between Lexington and Louisville and features eight distilleries producing Bourbon, which is the United States’ only native spirit and is produced only in Kentucky. You can visit one or two (I highly recommend Jim Beam and Maker’s Mark) or head to the Whiskey Heritage Center to try multiple brands in one spot.

If Bourbon isn’t your drink of choice, you can also visit several wineries in the area – there are over a dozen within an hour’s drive of Lexington. At Wildside Vines, about 20 minutes west of the city, you can sample eight of their award-winning wines at no cost. Be sure to try the creative dessert wines like Blueberry and Blackberry.

For a fun night on the town, try the Cheapside Bar and Grill, a local favorite tucked away on a side street in the downtown core. It’s always packed, the daily drink specials are a great deal, they often have live music on weekends, and the Kentucky Bourbon Ale is strong and cheap.

There are many familiar chain hotels in the downtown area and further out of the city, you can stay the night at several working horse farms that offer accommodation. For $55 a night, you can also try the Motel 6. It’s a five minute drive (or $10 taxi) out of the downtown core. It’s basic but clean, and with the money saved, you can afford a few more bottles of Bourbon or Kentucky wine for souvenirs.

Since I was born in Kentucky and still have family ties there, I perk up when the Kentucky Derby comes around. And, it’s come around. Every year at this time this race reminds me that the days of going to a race track are at hand. Since the Derby is in just a few hours, let’s head to Churchill Downs.

Churchhill Downs, although not the first racetrack in Kentucky, is probably the most famous. The first race track was built in Lexington in 1789. It wasn’t until 1875 when Churchill Downs came to be that the Kentucky Derby got its start. The growth of the race wasn’t particularly smooth with some years being a real financial bust. These days with the $25 general admission price tag, I imagine losing money is almost impossible.

One interesting feature about Churchill Downs is that there is a quarantine area for horses from other countries. Here’s a video that lets you take a peak. The guys who shot it tried to get some horse footage, but the horses are in shadows.

Another video shows Dominican, a horse that recently had a workhout getting his bath. Another shows the horse, Stormello working out on the track.

According to this commercial, Churchill Downs has been updated and it certainly gives an idea of what racing season is like in Louisville this time of year. The Derby isn’t the only day to head to the races. Check the Churchill Downs Web site for other race days and times.